The expedition of the freighter Kahana failed to return the Island to Widmore's possession. Shortly after its destruction, Jacob, according to Widmore, “convinced [him] of the error of [his] ways”. Charles worked to return the candidates to the Island and then returned himself in 2007 with Desmond Hume, aiming to stop the Man in Black from leaving. While on the Island, he died at the hands of his long-time rival Ben.

In the flash sideways world, Charles had a much better relationship with Desmond, Eloise and Daniel. As of the end of the series, he had yet to awaken and remember his life, and it is unknown when he eventually moved on.

Cunningham attempted to converse with Widmore in secret via Latin, but Juliet understood them, and revealed that all Others could speak Latin. She explained that the three soldiers were Others. When Cunningham tried to explain where their camp was to Juliet, Widmore killed him by snapping his neck then fled into the jungle. Locke refused to shoot him as, in Locke's words, "he's one of my people". He unknowingly led Locke's group to his camp. As Locke entered the camp, Widmore aggressively pointed a gun to Locke's head ordering him to stand down. After Locke won Richard's trust, Richard identified Widmore by name, telling him to lower his weapon. Locke then greeted Widmore, revealing knowledge of his first and last name, without saying how he knew him. This encounter with Locke seemed to inspire Widmore, since a man from the future knew who he was (although there is as of yet no evidence that Widmore was informed in 1954 that Locke was from the future). ("Jughead")

1977

When Kate and Sawyer handed the young, gut-shot Ben over to Erik, Widmore was mentioned. Erik indicated that Widmore would be unhappy with Ben's arrival, and implied that he was in some sort of leadership position at this time. ("Whatever Happened, Happened") After Richard took Ben to be healed at the Temple, Charles confronted Richard about his decision to help the boy, and his protests were only silenced by Richard's insistence that Jacob wanted them to help Ben. Charles entered the tent where young Ben was being kept and introduced himself. He told Ben that he had to return to living with the DHARMA Initiative, but he would still be "one of us." ("Dead Is Dead")

After Daniel Faraday was shot in the Other's camp Charles approached Jack on his horse and knocked him out with his rifle's butt. Charles brought Jack and Kate captive to the Other's camp and Richard explained the situation to him. Widmore inquired why the DHARMA Initiative people would declare war on them, but Eloise told him that the three intruders were not DHARMA people. Widmore then took notice of Daniel's body and remarked that he looked familiar. As Eloise informed Widmore that she was taking Jack and Kate to the bomb, he began to argue with her and rejected the idea but eventually gave in. ("Follow the Leader")

Later years

During his time as leader of the Others, Widmore made routine trips off the Island. During one of those trips, he fathered Penny with an unknown woman who lived in the outside world.

In 1988, Widmore assigned Ben and Ethan to kill Danielle Rousseau. When Ben returned to camp with Rousseau's baby, Alex, he was angrily confronted by an aging Widmore, who demanded to know why Ben was holding a baby. Ben was angered that Widmore had not informed him of the baby prior to accepting the mission. Widmore demanded that Ben kill her, claiming it to be the will of Jacob. Ben refused, and instead proposed that if it were indeed the will of the Island, Widmore should be able to kill her instead. Scoffing, Widmore turned his back and walked away, leaving Ben holding the baby. ("Dead Is Dead")

As leader of the Others, it is presumed that Widmore played an active role in the purge of the DHARMA Initiative in December 1992. However it is still unclear where he stands on the event, although Ben claimed that it was "the leader's" decision to kill the Initiative members. ("Cabin Fever") It is currently unknown whether he meant Widmore or Jacob. It should be noted that since Ben is a known liar, this might not be necessarilly true.

Some time after the Purge, Ben had Widmore exiled from the Island and supplanted him as leader of the Others. As Widmore was led to the submarine by armed guards, Ben came to say farewell. Widmore, however, felt Ben had come to "gloat" about his victory in having him exiled. Widmore had been exiled for "breaking the rules": namely, for regularly leaving the Island, and for having a family off the Island (specifically, a "daughter with an outsider"). Widmore scornfully told Ben that one day he would have to choose between Alex and the Island. He was then led to the submarine and exiled. ("Dead Is Dead")

Off the Island

Off the Island, Charles Widmore became known as a prolific entrepreneur and an executive at his own company, Widmore Industries. Little is known about when or how he acquired his business empire.

Although Charles was apparently not involved in the upbringing of his son Daniel (and never told Daniel that he was his father), he did bankroll Daniel's research at Oxford, and when Daniel's girlfriend Theresa Spencer suffered catastrophic psychological damage as a result of one of Daniel's experiments, Charles took responsibility for her care.

Relationship with Desmond

Charles was visited by Desmond Hume, who intended to ask Charles for his daughter's hand in marriage. Charles, under the impression that Desmond was looking for a job, looked over his resume, noting Desmond's job as a theatrical set designer, as well as Desmond's failure to graduate from university. After Desmond took note of Widmore's beautiful model of a boat, Widmore informed him of a solo race around the world that his company was sponsoring. He offered Desmond a job in his administrative department, after which Desmond told him that he had not come looking for a job, but instead wanted Charles's permission for himself and Penny to wed. Though noting that Desmond was making a noble gesture, Widmore stated that Desmond was unworthy of marrying his daughter, because he would never be a "great man," using Anderson MacCutcheon, the namesake of a brand of whiskey, as an example of a great man. Desmond then left, saddened and ashamed. ("Flashes Before Your Eyes")

In 1996, Widmore purchased the journal of the first mate of the Black Rock, a 19th century British slave ship, at a Southfield's auction. Desmond found him at the auction, demanding to know Penny's new contact information. Widmore asserted that it was Desmond's cowardice that separated Desmond from Penny. Desmond asked why Widmore hated him; Widmore retorted that it wasn't he who hated Desmond. He then gave Desmond Penny's address. ("The Constant")

Widmore's disapproval of his daughter's relationship with Hume led to his interception of letters that Desmond wrote to Penelope while serving time in a military prison. ("Live Together, Die Alone, Part 2")

Widmore sent the freighter Kahana to the Island, hiring Gault to captain the expedition, and telling him that, in fact Ben had planted the wreckage of Flight 815. ("Ji Yeon") He also hired Martin Keamy to lead a mercenary team to breach the Island, locate and apprehend Benjamin Linus, and, according to Ben, kill every other living person on the Island, including the survivors of Oceanic Flight 815, if Keamy's team found that they existed. ("Meet Kevin Johnson")

On the day the fake wreckage was discovered and shown on television, Charles paid a visit to Daniel in Essex, Massachusetts. He told Daniel that the wreckage shown on television was a fake, and that he knew this because he had planted it himself. He then offered Daniel an opportunity to travel to the Island, telling him that the Island's unique properties would allow him to further his research, and suggesting that the Island could heal the memory problems Daniel had been experiencing ever since his accident at Oxford. ("The Variable")

After the rescue of the Oceanic Six

Season 4

Sometime after the Oceanic Six were rescued, Widmore was confronted by Ben in his London penthouse. Widmore looked tired and unshaven, and when asked by Ben when he started "sleeping with a bottle of scotch by the bed", he replied "When the nightmares started." Widmore assumed that Ben had come to kill him, but Ben replied, "We both know I can't do that." The two argued about who was responsible for the death of Alex. Widmore claimed that everything Ben had he took from him. Ben threatened to kill Widmore's daughter, Penelope, whom Widmore indicated would be never found. Widmore claimed the Island was his but Ben asserted that he would never find it. Widmore mused that the hunt was on for both of them. ("The Shape of Things to Come")

It was shortly after this that Widmore's surveillance in Tunisia caught John Locke lying in the desert after having been transported there. Widmore had cameras fixed on this spot because he somehow knew it to be "the exit" from the Island. Widmore's associates found Locke and brought him to a field hospital. After he awoke, Locke found himself face-to-face with Widmore. Widmore reminded Locke of their meeting in 1954, which for Locke had only been 4 days ago. Widmore told Locke of an approaching war and agreed to help him in his quest to bring the Oceanic Six back to the Island.

He gave Locke his cover identity of Jeremy Bentham and provided Locke with the services of Matthew Abaddon, as well as dossiers on the whereabouts and status of the Oceanic Six. Before they parted Locke recalled that Widmore had previously wanted to kill everyone of the Island and was now helping him, but Widmore - likely recalling his conversation with Jacob - assured Locke this was no longer the case.("The Life and Death of Jeremy Bentham")

Some time later, Sun approached Widmore in London. At first he pretended to merely know her through his connection with her father. However, Sun confronted him, indicating that he knew she was part of the group that had been on the Island and that they were lying about it. Sun then offered to collaborate with Widmore. He asked her why she would want to help him, but she didn't answer. ("There's No Place Like Home, Part 2")

Season 5

While Sun was checking in for her flight to Los Angeles, the attendant asked her to hold for a moment, then escorted her to a room where the door was locked behind her. Widmore appeared and scolded her for approaching him in broad daylight in front of his colleagues. He brought up her statement about their common interests, and asked what they are. She told him plainly, "To kill Benjamin Linus." ("Because You Left")

Shortly thereafter, in his office, Widmore was surprised by an unexpected visitor: Desmond Hume, whom he had not seen in around seven years. Desmond demanded to know where he could find Daniel Faraday's mother. When Widmore appeared confused, Desmond revealed that he knew Widmore had subsidized Faraday's research at Oxford for about ten years before he sent Daniel to the Island on the freighter, and also paid for Theresa's medical support. Widmore attempted to find out whether Penny was safe, yet Desmond insisted on a location for Faraday's mother.

Widmore eventually gave Desmond an address in Los Angeles, yet warned Desmond that he was "getting (himself) involved in something that goes back many many years." and begged Desmond to keep himself and Penny out of it by hiding. ("Jughead")

A few days later, as Widmore was walking out of Widmore Industries, Ben phoned him from a marina in Long Beach. He told Widmore that he was about to return to the Island, to which Widmore replied that the Island wouldn't let him. Ben reminding Widmore that he was going to murder his daughter Penelope, and that he was staring at Desmond's boat. Widmore responded, "You wouldn't dare," as Ben hung up. Ben ended up shooting Desmond, but hesitated to kill Penny, giving the injured Desmond enough time to stop him. ("Dead Is Dead")

Widmore receives a phone call from Ben, informing him of his intentions to kill Penny. ("Dead Is Dead")

After this, Charles traveled to Los Angeles and appeared at the Long Beach hospital where Desmond was being treated for his gunshot wound. Here, he met up with his old friend, Eloise Hawking, who informed him that Desmond was recovering, to which he indicated that he was pleased, and Penny was inside and that he should go see her. Charles stated that he had sacrificed his relationship with Penny. It is then revealed that Eloise knew that sending Daniel to the island would lead to his death, stating that it was she who had made a sacrifice. Charles interrupts her saying "He was my son too, Eloise." Angered by this remark, Eloise slapped Charles in the face and walked off. ("The Variable")

Return to the Island (Season 6)

Widmore managed to take Desmond from the hospital, while he was still unconscious. Having been told by Jacob of how Desmond survived a catastrophic electromagnetic event in the past, Widmore planned to check if Desmond could do it again, claiming that if he cannot they will all die. ("Happily Ever After") He and his crew took Desmond back to the Island via a submarine. ("Dr. Linus")

After seeing the activity on the beach camp, Widmore's submarine docked at Hydra Island and set up a perimeter using a sonar pylon similar to the sonar fence once employed by the DHARMA Initiative. Widmore's team, led by Zoe, captured Sawyer after he threatened her and took him to the submarine. When Sawyer was brought to Widmore's cabin, Widmore and Sawyer made an agreement that if Sawyer brought the Man in Black to Widmore, then Sawyer and his friends could safely leave the Island. ("Recon")

After the Man in Black temporarily left his group to try and recruit Sun, a team of Widmore's people attacked the group with tranquillizer darts and captured Jin. The next day, the Man in Black came to Hydra Island in an outrigger and discovered that Widmore had already set up a sonar fence around the perimeter of the island, preventing the Man in Black from coming in. Widmore's men appeared and led the Man in Black further down the beach to a meeting with Widmore himself. Widmore asked the Man in Black whether he knew who he was. The Man in Black did, and then asked Widmore whether he knew who the Man in Black was. Widmore guardedly answered that the Man in Black obviously wasn't John Locke. The Man in Black said that he had come because Widmore had taken one of his people, Jin. Widmore denied knowing anything. The Man in Black ominously said that the war Widmore once foretold to Locke "just got here."

Later, in the Hydra station, Widmore berated Zoe for making a move ahead of their planned schedule. Noticing that Jin was in the room, Widmore gave him a camera containing pictures of Jin's daughter, Ji Yeon, that Widmore had found amongst Sun's luggage in the Ajira plane. Widmore told Jin that he, too, had a daughter and knows how it feels to be kept apart. He went on to say that Jin's reunion with his daughter would be short-lived if "that thing" (the Man in Black) ever got off the Island, because everything they knew and loved would "cease to be." Widmore claimed he had come to the Island in order to stop the Man in Black from escaping. When Jin asked Widmore what his next move was going to be, Widmore announced that it was time for Jin to see the package, which he said was a "who," not a "what." ("The Package")

When Widmore was later talking to a confused Desmond, who thought he was still in the hospital and that Zoe was a nurse, he told him he had come back to the Island. This made Desmond mad, so he then began banging Widmore's head with an IV stand. Widmore's response was the same as Eloise's, "The Island isn't done with you, Desmond". After leaving the room, Jin asked what Desmond is doing on the Island. Widmore replied that it would be easier to show Jin and ordered Zoe to take him to the generator room, despite Zoe's protests about the tests not being scheduled until tomorrow. Simmons is accidentally killed in the solenoid chamber as the test was set-up. Widmore looked sadly at Simmons' dead body as he is taken out and ordered that Desmond be placed inside. He insisted that Desmond would be fine if what he has heard about him is true. He then tells Desmond that once the experiment is over, Desmond will have to make a sacrifice. Desmond cynically asked what Widmore knows about sacrifice. Widmore angrily told him about his son dying, his daughter hating him and him never seeing his grandson, all in the name of the Island. Unless Desmond can help him, he said that all that would have been for nothing and Penny, Desmond's son and everyone else will be dead. Desmond was then exposed to the electromagnetism inside the chamber, which he survives, being left unconscious for only a few seconds. Widmore offered to explain why he had to put Desmond through that, but Desmond declined and cooperatively asked when they start with whatever is so important. ("Happily Ever After")

After Desmond had been captured by Sayid and the Man in Black, Widmore sent Zoe to the Man in Black's camp on the main island to deliver an ultimatum for the Man in Black to return Desmond. When Sawyer and other Survivors arrived on Hydra Island, Widmore instructed Zoe to tell Sawyer that their deal was off and ordered firing on the Man in Black's group, having arrived on a beach on the main island, resulting in casualties of the Man in Black's group. ("The Last Recruit")

Widmore threatens to kill Kate.

Widmore lead Kate, Sawyer, Sun, Jin, Hurley, Claire and Frank to the Hydra station with his team. After Sawyer refused to go in the cages, again and seizes a rifle from Seamus, Widmore grabbed Kate and threatened to kill her but when Sawyer tried to call his bluff, Widmore informed them that he had a list of names including "Ford, the Kwons, and Reyes but not Kate Austen" and that so it didn't matter to him whether she lived or died. Widmore approached Sawyer and added that he was doing this for Sawyer's own good. Widmore checked with his men whether the fence was live yet.

That night, the Man in Black murdered much of Widmore's team in his black smoke form, and the following day - in the form of Locke - killed two guards on the Ajira flight. More of Widmore's team were killed and injured in a shoot-out at the submarine dock with the remainder of Jacob's candidates who attempted to commander the submarine and escape from the Island. ("The Candidate")

Shortly after the destruction of his submarine, Widmore showed up at the Barracks with Zoe. They intercepted Richard, Miles, and Ben as they were preparing to leave to destroy the Ajira airplane with a backpack full of C4. Widmore explained that he'd already loaded the plane with explosives. When questioned further, he said that he had been invited back to the island by Jacob himself. Before he could elaborate further, Zoe spotted the Man in Black arriving by outrigger.

As Miles ran off into the jungle and Richard went to talk with the Man in Black, Widmore and Zoe hid themselves in the secret room behind Ben's bookcase. After throwing Richard out of the way, the Man in Black asked Ben about Widmore's whereabouts, which Ben revealed after being promised that he would have the island all to himself after the Man in Black escaped. The Man in Black went to the secret room and began to question Widmore and Zoe, but Widmore admonished Zoe for speaking and the Man in Black cut her throat, declaring her to be useless.

The Man in Black then threatened to kill Widmore's daughter Penny once he escapes the island, unless Widmore spoke voluntarily. Widmore agreed at first, afraid for the life of his daughter and having no other alternative. He explained that he brought Desmond back to the island because of his resistance to electromagnetism. He then refused to give up any other information while Ben was listening. The Man in Black then instructed Widmore to whisper the answers in his ear, which he did until Ben shot him repeatedly with a handgun. ("What They Died For")

The information Widmore whispered into the Man in Black's ear was kept private for several hours. After returning to the well where he threw Desmond and discovering that he'd escaped, he explained to Ben that Widmore told him that Desmond was Jacob's "last resort", a trump card to be used if all of Jacob's other Candidates were to die.
("What They Died For")

Charles heard that Charlie Pace, who was expected to play music alongside his son at Eloise's charity event was arrested for possessing drugs. Intent to get Charlie to perform at the event, as his Eloise would "destroy" him otherwise, Widmore requested that his trusted employee Desmond Hume help. Desmond understood Widmore wanted him to "babysit" Charlie. While he believed it was beneath Desmond, he wanted someone he could trust to handle the situation. Desmond was happy to help. Widmore praised Desmond's life free of family and commitments and shared his MacCutcheon whisky, saying nothing is too good for Desmond. Desmond failed to keep hold of Charlie, after Charlie caused a car accident. Despite the circumstances, Widmore got mad over Desmond's failure and insisted, he explain it to Eloise if he doesn't think it's a big deal. ("Happily Ever After")

Charles Widmore remained unaware of his death and did not move on. It is likely that he moved on at a later time with his wife and son.

Trivia

Widmore appeared to be aware of the conflict between Jacob and the MiB. ("The Package")

Bram, who appeared to side with Jacob tried to talk Miles out of working for Widmore, telling him that "He's playing for the wrong team." However, this was presumably before Widmore's "conversion". ("Some Like It Hoth")

Charles never appeared in a scene with his daughter, Penny, even though the two characters appeared in the same episode multiple times.

He met Richard, Sawyer, Juliet, and Locke (for the first time) in 1954 on the Island. He met Ben, Jack, and Kate in 1977 on the Island. He met Desmond in 1996 off the Island. He was first shown (chronologically) meeting Daniel in 2004, though he is Daniel's father off the Island. He met Sun in late 2007 off the Island. He met Jin, Hurley, Claire and Frank in 2007 on the Hydra Island. He met Miles in 2007 on the Island.

In Homer's Odyssey, Poseidon was the God of the Sea. He hated Odysseus and used his powers over the ocean to hinder Odysseus's attempts to return to Penelope, his wife. Charles Widmore does not want Desmond to be with Penelope, and "controls the sea" with his freighter, Kahana, which resides off the Island's coast. It's possible that Charles Widmore is a Poseidon figure in that he controls the sea around the island and is hindering Desmond's attempts to be with Penelope. It also seems that Ben is an Odysseus figure, someone who uses exceptional cunning to attain his goals, and, post Island moving, Ben is indeed in search of Penelope, who is under Widmore's protection. The Poseidon/Odysseus analogy brings to mind themes of force versus reason.

Desmond seems more likely as a stand-in for Odysseus in this scenario, as it is his quest to be with Penny that Widmore hinders most.

Ben is seen reading Ulysses on Ajira Flight 316 in "316". Ulysses is a novel by James Joyce. The title alludes to Odysseus (Latinised into Ulysses) and there are many parallels, both implicit and explicit, between the two works.

Charles is of Old Norse origin, and its meaning is "free man". From "karl", similar to Old English "churl", meaning "man, serf". Today the word has similar meaning in Swedish and Icelandic.

Karl was a name reserved for kings in Sweden. Sweden's current king is Carl XVI Gustaf.

When Desmond is interviewed in the office of Charles Widmore, there is a picture of a polar bear and an image of a Buddha on the wall. On the top of the picture, the word "Namaste" appears. This same painting appears in "Jughead".

In the DVD commentary for "The Constant", Damon Lindelof described Widmore as "the big bad" of the show. This term originated with Buffy the Vampire Slayer, which used it to describe each season's main villain. The role of "big bad" was eventually taken over by the Man in Black.

In the casting call for young Widmore, he was described as "Nigel. British, in his late teens. Smart and mature for his age, if a little rough around the edges."[1] It may be noted however, that actor Alan Dale uses his native New Zealand accent in his portrayal of Widmore or, at the very least, does not successfully hide his true origin.

In the casting call for middle-aged Widmore he was described as "Graham, Caucasian, male, 40. Blue eyes, 6 foot, English/British ONLY, confident, has come into his own and ready to be a leader. He's the SVP of a major financial corporation jockeying for the CEO position..."[2]